119-62-0

Basic information

• Product Name: 2-Amino-1-(4-nitrophenyl)-1,3-propanediol
• Synonyms: 2-Amino-1-(4-nitrophenyl)-1,3-Propanediol (DL-);2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL(DL-)/S-BASE;NSC163951;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol;2-Amino-1-(4-nitrophenyl)-1,3-propanediol;1-(p-Nitrophenyl)-2-amino-1,3-propanediol;2-Amino-3-(4-nitrophenyl)-1,3-propanediol;D-(-)-Three-1-[4-Nitrophenyl]-2-AMino-1,3-Propanediol
• CAS NO: 119-62-0
• Molecular Formula: C₉H₁₂N₂O₄
• Molecular Weight: 212.20258
• EINECS: 204-338-1
• Mol File: 119-62-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: 163-165 °C
• Boiling Point: 451.881 °C at 760 mmHg
• Flash Point: 227.09 °C
• Appearance: light yellow crystal power
• Density: 1.411 g/cm³
• Vapor Pressure: 5.92E-09mmHg at 25°C
• Refractive Index: 1.63
• PKA: 10.98±0.45(Predicted)
• CAS DataBase Reference: 2-Amino-1-(4-nitrophenyl)-1,3-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-1-(4-nitrophenyl)-1,3-propanediol(119-62-0)
• EPA Substance Registry System: 2-Amino-1-(4-nitrophenyl)-1,3-propanediol(119-62-0)

Safety Data

• Hazardous Substances Data: 119-62-0(Hazardous Substances Data)

Usage

General Description

2-Amino-1-(4-nitrophenyl)-1,3-propanediol is a chemical compound with the molecular formula C9H12N2O5. It is an amino alcohol that contains a 1,3-propanediol backbone with an amine and nitrophenyl substituent. 2-Amino-1-(4-nitrophenyl)-1,3-propanediol is commonly used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also utilized in the production of dyes and pigments. The presence of the nitrophenyl group gives the compound its characteristic yellow color, making it useful as a colorant in various applications. Additionally, 2-Amino-1-(4-nitrophenyl)-1,3-propanediol has been studied for its potential biological activities, such as antimicrobial and antifungal properties.

InChI:InChI=1/C9H12N2O4/c10-8(5-12)9(13)6-1-3-7(4-2-6)11(14)15/h1-4,8-9,12-13H,5,10H2

Upstream product

• 1194757-37-3 (2S,3S)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester 
• 582295-24-7 (2S,3R)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 99170-59-9 syn-(2R,3R)-[2-amino-3-methoxy-3-(4-nitrophenyl)-1-propanol] 
• 903506-87-6 (1R,2R)-2-amino-3-methoxy-1-(4-nitro-phenyl)-propan-1-ol 
• 3123-13-5 N-[1-hydroxymethyl-2-(4-nitro-phenyl)-2-oxo-ethyl]-acetamide 
• 100254-93-1 N-[(1RS,2RS)1-hydroxymethyl-2-methoxy-2-(4-nitro-phenyl)-ethyl]-acetamide 
• 99170-59-9 (2RS,3RS)-2-amino-3-methoxy-3-(4-nitro-phenyl)-propan-1-ol 
• 1885-08-1 (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 108943-99-3 N-(1-acetoxy-3-oxo-3-phenylpropyl)acetamide 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 3509-75-9 (1RS,2RS)-1,3-diacetoxy-2-acetylamino-1-phenyl-propane 
• 33485-02-8 (1RS,2RS)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane 
• 74104-28-2 α-acetamido-β-hydroxypropiophenone 

Downstream Products

• 106378-64-7 (1RS,2RS)-2-furfurylidenamino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 139662-06-9 (1S,2S)-1-(4-nitro-phenyl)-2-[2]thienylmethylenamino-propane-1,3-diol 
• 139662-06-9 (1R,2R)-1-(4-nitro-phenyl)-2-[2]thienylmethylenamino-propane-1,3-diol 
• 61904-25-4 N,N'-bis-[2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-oxalamide 
• 76567-25-4 [(1RS,2RS)-2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-oxalamic acid methyl ester 
• 99860-58-9 (1R,2R)-2-amino-3-dichloroacetoxy-1-(4-nitro-phenyl)-propan-1-ol 
• 97723-45-0 (1RS,2RS)-1,3-bis-dichloroacetoxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propane 
• 56-75-7 chloramphenicol 
• 56-75-7 2-(2,2-dichloroacetylamino)-1-(4-nitrophenyl)propane-1,3-diol 
• 56-75-7 chlorampenicol 
• 13838-08-9 Azidamfenicol 
• 10172-89-1 (R)-N-acetylphenylalanin 
• 2018-61-3 (S)-2-acetylamino-3-phenylpropanoic acid 
• 72-19-5 L-threonine 

Relevant articles and documents

Binding and action of triphenylphosphonium analog of chloramphenicol upon the bacterial ribosome

Chloramphenicol (CHL) is a ribosome-targeting antibiotic that binds to the peptidyl transferase center (PTC) of the bacterial ribosome and inhibits peptide bond formation. As an approach for modifying and potentially improving the properties of this inhib

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One-Pot Asymmetric Synthesis of an Aminodiol Intermediate of Florfenicol Using Engineered Transketolase and Transaminase

Florfenicol is the 3′-fluoro derivative of thiamphenicol and has been widely used in veterinary medicine for its high antibacterial activity and safety. However, the development of simplified and environmentally friendly catalytic methods for the stereoselective production of florfenicol is a key challenge. Herein, we established a highly stereoselective enzymatic one-pot reaction for the synthesis of an aminodiol intermediate of florfenicol bearing two stereocenters from industrial raw material 4-(methylsulfonyl) benzaldehyde by coupling transketolase (TK) and ω-transaminase (TA). The enantioselectivity of TK from E. coli was converted from (S) (93% ee) to (R) (95% ee), and we also inverted the enantiopreference (E(S) = 9 to E(R) = 12) and ketone/aldehyde substrate selectivity of TA ATA117 via structure-guided enzyme engineering. Docking calculations and molecular dynamics simulations of the wild-type and mutant enzymes unveiled the molecular basis for enzymatic stereocontrol. Using the engineered TK and TA, (1R,2R)-p-methylsulfonyl phenylserinol was biosynthesized with good yield (76%) and high stereoselectivity (96% de and >99% ee). Our work established an enzymatic synthetic route to (1R,2R)-p-methylsulfonyl phenylserinol, facilitating the development of a chemoenzymatic method for producing florfenicol.

Direct separation of a (1R,2R)-2-amino-1-(4-nitrophenyl)-1,3-propanediol in a resolution of its conglomerate

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Stereocontrolled synthesis of syn-β-hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide

β-Hydroxy-α-amino acids figure prominently as chiral building blocks in chemical synthesis and serve as precursors to numerous important medicines. Reported herein is a method for the synthesis of β-hydroxy- α-amino acid derivatives by aldolization of pseudoephenamine glycinamide, which can be prepared from pseudoephenamine in a one-flask protocol. Enolization of (R,R)- or (S,S)-pseudoephenamine glycinamide with lithium hexamethyldisilazide in the presence of LiCl followed by addition of an aldehyde or ketone substrate affords aldol addition products that are stereochemically homologous with L- or D-threonine, respectively. These products, which are typically solids, can be obtained in stereoisomerically pure form in yields of 55-98 %, and are readily transformed into β-hydroxy-α-amino acids by mild hydrolysis or into 2-amino-1,3-diols by reduction with sodium borohydride. This new chemistry greatly facilitates the construction of novel antibiotics of several different classes. On aldol: Enolization of (R,R)- or (S,S)-pseudoephenamine glycinamide with lithium hexamethyldisilazide (LiHMDS) in the presence of LiCl followed by addition of either an aldehyde or ketone substrate affords aldol addition products which are stereochemically homologous with L- or D-threonine, respectively. These products can be obtained in stereoisomerically pure form in yields of 55-98 %, and are readily transformed into β-hydroxy-α-amino acids by mild hydrolysis or into 2-amino-1,3-diols by reduction.